EP2085089A1 - Phospholipides contenant des acides gras oméga-3 pour le traitement du surpoids, de l'obésité et du comportement addictif - Google Patents

Phospholipides contenant des acides gras oméga-3 pour le traitement du surpoids, de l'obésité et du comportement addictif Download PDF

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Publication number
EP2085089A1
EP2085089A1 EP08101213A EP08101213A EP2085089A1 EP 2085089 A1 EP2085089 A1 EP 2085089A1 EP 08101213 A EP08101213 A EP 08101213A EP 08101213 A EP08101213 A EP 08101213A EP 2085089 A1 EP2085089 A1 EP 2085089A1
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composition
medicament
phospholipid
fatty acids
mpl
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EP08101213A
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German (de)
English (en)
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Ulrich Prof. Dr. Massing
Lenka Taylor
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KTB Tumorforschungs GmbH
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KTB Tumorforschungs GmbH
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
    • A61K31/6615—Compounds having two or more esterified phosphorus acid groups, e.g. inositol triphosphate, phytic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents

Definitions

  • the invention relates to the use of phospholipids containing ⁇ -3-fatty acids and/or containing low amounts of ⁇ -6 fatty acids, notably phospholipids of marine origin, for the treatment of overweight, obesity and addictive behavior.
  • body mass index (BMI) weight in kg/(height*height in m) > 25 is overweight; ⁇ 30 is obese).
  • BMI body mass index
  • the cause is a disproportion of energy uptake and energy consumption, the energy balance is positive over a prolonged period of time.
  • Appetite and eating behavior are regulated by various internal messengers and neurotransmitters.
  • the feeling of satiation is caused by expansion of the stomach which stimulates the nervus vagus , a big parasympathic nerve that passes the stimulus on to the hypothalamus.
  • Different neurotransmitters with anorectic effect are activated, for example Noradrenaline, Serotonine and neuropeptides as Glucagon-like Peptide (GLP-1) and ⁇ -Melanocyte-stimulating hormone ( ⁇ -MSH).
  • GLP-1 Glucagon-like Peptide
  • ⁇ -MSH ⁇ -Melanocyte-stimulating hormone
  • the hormone Ghreline activates orexigenic neurotransmitters in the hypothalamus, for example Neuropeptide Y (NPY) and Agouti-Related Peptide (AgRP), antagonizing ⁇ -MSH, as well as Anandamide, a endogenous agonist of the Cannabinoid-1-receptor (CB1).
  • NPY Neuropeptide Y
  • AgRP Agouti-Related Peptide
  • Anandamide a endogenous agonist of the Cannabinoid-1-receptor
  • CB1 receptors are widespread in the mammalian brain.
  • the main agonist known is Tetrahydrocannabinol (THC), a lipophilic component of the plant cannabis sativa .
  • THC is well known to have an - among others - appetite stimulating effect.
  • the synthetic analogon Nabilon is used to stimulate appetite in patients suffering from AIDS- or tumor-induced cachexia.
  • Another effect of cannabinoid receptor stimulation is the activation of dopaminergic pathways in the mesolimbic system, the so called “reward system” which is known to cause addictive behavior and "craving" in animals and humans.
  • the stimulation of these reward mechanisms leads to an excessive intake of food, preferentially high in fat and dense in energy as well as craving for nicotine or alcohol in addicted people.
  • a selective antagonist has recently been developed as treatment of obesity in humans.
  • the substance is known as Rimonabant and obtained approval as anti-obesity, appetite reducing drug under the name Acomplia ® in Europe in 2006. Its effect is the blocking of CB1 receptors, so that endogenous agonists can not stimulate the receptor and the orexigenic and/or reward signal will not be transmitted.
  • rimonabant has been evaluated in several trials as supporting drug for smoking cessation.
  • the endogenous CB-receptor full agonists known today are Arachidonylethanolamide (Anandamide) and 2-Arachidonylglycerol (2-AG). Both derive from Arachidonic Acid (AA), an Omega-6-fatty acid which is taken up in high amounts with food from mammalian origin, like meat and eggs.
  • AA Arachidonic Acid
  • AA is essential for the human organism as it is an important precursor for lipid messengers, not only Anandamide and 2-AG, but also prostaglandins, for example PGE2, and leukotrienes, which are responsible for inflammatory processes.
  • PGE2 is the most prominent member of the prostaglandin family, this messenger is responsible for the initiation and prolongation of the inflammation response as well as pain and metastatic processes. In order for AA to be transformed into these lipid messengers, it needs to be cleaved enzymatically out of a phospholipid molecule building the cellular membrane.
  • Phospholipids are a main component of cellular membranes. They consist of a hydrophilic head group which is connected to the hydrophobic molecule part via a phosphate group. Their structure is as follows: wherein X can be among others choline, serine, glycerol, ethanolamine "PG (Phosphatidylglycerol)" and inositol, R1 and R2 can be the O-acyl-remnants of fatty acids. R2 usually is the position that binds a long chain unsaturated fatty acid like for example AA.
  • PL of marine origin are extracted from water animals and preferentially from caviar, and represent glycerophospholipids with various headgroups and a high percentage of ⁇ -3-fatty acids building the hydrophobic part.
  • ⁇ -3-fatty acids namely eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • Fig. 1 shows FA-pattern changes in plasma PL (A) and whole blood lymphocytes (B) after 6 weeks of MPL intake.
  • aspects (1) to (6) of the invention are based on the finding that the administration of phospholipids containing ⁇ -3-fatty acids and/or containing low amounts of ⁇ -6 fatty acids, notably phospholipids of marine origin (MPL) to overweight or obese people leads to a reduction of appetite and body weight.
  • MPL phospholipids of marine origin
  • predictive behavior refers to people with nicotine, alcohol, medicament, etc. addictive behavior.
  • phospholipid and "at least one phospholipid” include phospholipids derived from natural resources and synthetic phospholipids.
  • "MPL” and "phospholipids of marine origin” according to aspect (2) of the invention refer to phospholipid derived from water animals such as fish, and most preferably is isolated from fish liver or roe. Particular preferred MPL are those of aspect (3) of the invention.
  • said at least one phospholipid or MPL of the composition or medicament according to aspects (1) to (4) and (6) of the invention contains no or only low amounts of ⁇ -6 fatty acids, preferably no or only low amounts of arachidonic acid.
  • the composition or medicament contains ⁇ -3-fatty acids, preferably eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA).
  • Said at least one phospholipid is selected from 1,2-diacylglycerophospholipids, 1-acylglycerophospholipids and 2-acylglycerophospholipids having saturated and/or unsaturated acyl residues or pharmacologically acceptable salts thereof.
  • said at least one phospholipid preferably contains acyl residues selected from saturated acyl residues, v-3- and ⁇ -9-fatty acid residues and mixtures thereof, and the content of said acyl residues preferably is at least 75% by weight, preferably at least 90% by weight, most preferably at least 96% by weight of the total acyl residues present within the phospholipid. It is moreover preferred that said at least one phospholipid is a phosphatidylcholin.
  • said at least one phospholipid is comprised in the composition or medicament in an amount of 5 to 100% by weight, preferably 30 to 100% by weight (basis total weight of the composition or medicament).
  • the composition or medicament further contains triglycerides, free fatty acids diglycerides and/or monoglycerides, wherein the total content of said further glycerides and fatty acids is no more than 95% by weight, preferably no more than 90% by weight, most preferably no more than 75% of the total lipids of the composition or medicament.
  • the composition or medicament contains oils, preferably fish oils.
  • composition or medicament further comprises an oil having a high content of ⁇ -3-fatty acids.
  • R 1 und R 2 are independently selected from H and unsubstituted C 16-24 acyl residues, which may be saturated or unsaturated, and X is selected from a choline, serine, ethanolamine and inositol residue.
  • At least one of R1 and R2 is an ⁇ -3-fatty acid residue having at least 20 C-atoms such as an eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) residue or is an ⁇ -9-fatty acid residue having at least 18 C-atoms such as an oleic acid, erucic acid or nervonic acid residue. It is also preferred that the content of ⁇ -3- and ⁇ -9-fatty acid residues is at least 20 %, preferably at least 35 %, most preferably at least 45 % by weight of all acyl residues of the phospholipid/MPL. Finally it is preferred that the weight ratio of ⁇ -3-fatty acids and/or ⁇ -9-fatty acids to ⁇ -6-fatty acids in the MPL is at least 10 : 1, most preferably at least 15 : 1.
  • Particularly preferred phospholipids/MPLs of the present invention include Di-DHA-, Di-EPA-, Di-Oleyl-, EPA/DHA-, hydrated egg- and soja-phosphatidylcholines.
  • the phospholipids are the sole pharmacologically or dietetically active ingredient of the composition or medicament.
  • the composition or medicament further contains pharmacologically functional compound.
  • functional compounds are selected from compounds for the treatment of obesity or addictive behavior including cannabinoid-receptor antagonists such as Rimonabant (5-(4-chlorphenyl)-1-(2,4-dichlorphenyl)-4-methyl-N-piperidinopyrazol-3-carbamid) and Taranabant (N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[[5-(trifluoromethyl)pyridin-2-yl]oxy]propanamide); satiation enhancers/appetite suppressants including amphetamines that stimulate the release of katecholamines or inhibit the re-uptake such as diethylpropion, mazindol, phentermin, phenylpropanolamin or the like, preferably low-dosed amphetamines
  • composition or medicament additionally contains dietary fibers and swelling agents such as chitosans, cellulose derivates, Pektines, mucilages, alginates, chitin derivatives, L-carnitin or pyruvat.
  • dietary fibers and swelling agents such as chitosans, cellulose derivates, Pektines, mucilages, alginates, chitin derivatives, L-carnitin or pyruvat.
  • the amount of such pharmacologically functional compounds preferentially may be in the range of 1 to 99% by weight relative to the phospholipids/MPLs of the composition or medicament of the invention.
  • composition, medicament or food supplement of aspects (1) to (6) above may further contain pharmaceutically and dietetically acceptable carriers, binders, excipients, diluent, etc.
  • composition, medicament or food supplement of aspects (1) to (6) above is preferably in the form for oral administration (e.g. in the form of a tablet, capsule or the like). In case of aspects (1) to (4) and (6) it may also be in the form for intravenous administration.
  • the amount of pharmaceutical compositions or medicament, or food supplement of aspects (1) to (5) to be administrative to a patient, or the amount of composition administered to a patient according to the method of aspect (6) is within the ambit of the skilled practitioner, and generally lies within the range of 1 to 100 mg of the composition per kg bodyweight per day, which corresponds to a range of 0.3 to 30 mg of the phospholipid containing ⁇ -3-fatty acids and/or containing no or only low amounts of ⁇ -3-fatty acids per kg bodyweight per day.
  • the fatty acid pattern of cellular membranes can be altered by offering PL or their so called "lyso" form, where one of the fatty acid is cleaved enzymatically out of the PL molecule.
  • the lyso-PL are taken up into the cellular membranes and reacylated with another fatty acid to form a new membrane PL.
  • the uptake of fatty acids into the brain across the blood brain barrier takes place in a similar way, namely by uptake of the lyso-PL Qi K. et al.; Curr Opion Clin Nutr Metab Care 2002, 5(2): 133-138 .
  • phospholipids notably marine phospholipids induces a reduction of AA in cellular membranes and therefore lead to a decreased level of endogenous CB1 receptor agonists deriving from AA.
  • stimulation of CB1 receptors takes place only in a limited fashion, there are less orexigenic signals and the reward system is not over stimulated anymore.
  • the expected effect in mammals is less appetite and craving either for food and therefore facilitated weight reduction or for nicotine or alcohol and facilitated cessation.
  • Example 2 Change of fatty acid pattern of tumour cells in vitro
  • tumour cell lines LNCaP, AsPC1 and Du145 available as CRL-1740, HTB-81 and CRL-1682, respectively, from American Type Culture Collection (ATCC), Rockville, Maryland, USA
  • DMEM Dulbecco's Modified Eagle Medium from Gibco Invitrogen, Germany, Ord.No. 61965-026
  • BSA Bovine Serum Albumine from Sigma, Germany, Ord.No. A9418-100
  • C16:0-lysoPC 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (C16:0-lysoPC) from Sigma, Germany, Ord. No.
  • C17:0-lysoPC (1-heptadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (C17:0-lysoPC) from Avanti Polar Lipids, USA, Ord.No. 8556676P) at a concentration of 450 ⁇ M, respectively.
  • the amounts of palmitic acid (C16:0), heptadecanoic acid (C17:0) and arachidonic acid (AA) in percent of total fatty acid in cell membranes are shown in the following Tables 1 and 2.
  • Table 1 C16:0 LPC administration Cell line Annotation C16 (%) AA (%) LNCaP without C16-LPC 34.9 5.2 72h C16-LPC 58.2 1.9 AsPC1 without C16-LPC 21.7 3.5 72h C16-LPC 65.6 2.3 Du145 without C16-LPC 25.8 5.9 72h C16-LPC 47.4 4.5
  • Table 2 C17:0 LPC administration Cell line Annotation C17 (%) AA (%) LNCaP without C17-LPC 13.4 4.5 72h C17-LPC 58.8 2.2 AsPC1 without C17-LPC 6.3 3.7 72h C17-LPC 57.5 2.3 Du145 without C17-LPC 7.7 6.1 72h C17-LPC 54.9 4.8
  • Example 3 Changes of fatty acid pattern in human blood

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EP08101213A 2008-02-01 2008-02-01 Phospholipides contenant des acides gras oméga-3 pour le traitement du surpoids, de l'obésité et du comportement addictif Withdrawn EP2085089A1 (fr)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011050474A1 (fr) 2009-10-29 2011-05-05 Acasti Pharma, Inc. Compositions de phospholipides thérapeutiques concentrées
FR2955461A1 (fr) * 2010-01-27 2011-07-29 Polaris Ingredient nutritionnel riche en dha et epa
WO2012112520A1 (fr) * 2011-02-16 2012-08-23 Pivotal Therapeutics, Inc. Préparations comprenant des acides gras oméga-3 et un agent anti-obésité pour la réduction du poids corporel chez les patients atteints d'une maladie cardiovasculaire et chez les diabétiques
WO2012155094A1 (fr) * 2011-05-12 2012-11-15 Mycell Technologies, Llc Formulations de phospholipide comprenant des acides gras oméga
WO2013122622A1 (fr) * 2012-02-14 2013-08-22 Pivotal Therapeutics, Inc. Méthode pour traiter l'obésité à l'aide de formulations anti-obésité et d'acides gras oméga-3 pour la réduction du poids corporel chez des patients atteints de maladies cardiovasculaires (mcv) et des diabétiques
US8952000B2 (en) 2011-02-16 2015-02-10 Pivotal Therapeutics Inc. Cholesterol absorption inhibitor and omega 3 fatty acids for the reduction of cholesterol and for the prevention or reduction of cardiovascular, cardiac and vascular events
US8951514B2 (en) 2011-02-16 2015-02-10 Pivotal Therapeutics Inc. Statin and omega 3 fatty acids for reduction of apolipoprotein-B levels
US9119826B2 (en) 2011-02-16 2015-09-01 Pivotal Therapeutics, Inc. Omega 3 fatty acid for use as a prescription medical food and omega 3 fatty acid diagniostic assay for the dietary management of cardiovascular patients with cardiovascular disease (CVD) who are deficient in blood EPA and DHA levels
EP2930246A1 (fr) 2014-04-07 2015-10-14 QIAGEN GmbH Nouveaux polymorphismes nucléotidiques simples associés à diverses maladies et troubles
US10631564B2 (en) 2015-06-19 2020-04-28 University Of Southern California Enterically coated microparticle compositions and methods for modified nutrient delivery
US10744070B2 (en) 2015-06-19 2020-08-18 University Of Southern California Enteral fast access tract platform system
WO2020177728A1 (fr) * 2019-03-05 2020-09-10 四川国为制药有限公司 Composition d'acides gras et leur application
CN111902053A (zh) * 2017-12-21 2020-11-06 阿克海洋生物南极股份公司 溶血磷脂酰胆碱组合物
US11744869B1 (en) * 2023-01-05 2023-09-05 King Abdulaziz University Compositions and methods for treatment of addiction withdrawal symptoms

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WO2007009819A1 (fr) 2005-07-22 2007-01-25 Ktb Tumorforschungsgesellschaft Mbh Acylglycerophospholipides pour traiter des troubles associes au cancer
EP1417211B1 (fr) * 2001-07-27 2007-05-30 Neptune Technologies & Bioressources Inc. Phospholipides naturels d'origine marine contenant des flavonoides et des acides gras polyinsatures, et leurs applications

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EP0404300A2 (fr) * 1989-06-22 1990-12-27 Tosoh Corporation Procédé de préparation de phospholipides contenant de l'acide eicosapentaénoique
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EP1417211B1 (fr) * 2001-07-27 2007-05-30 Neptune Technologies & Bioressources Inc. Phospholipides naturels d'origine marine contenant des flavonoides et des acides gras polyinsatures, et leurs applications
WO2007009819A1 (fr) 2005-07-22 2007-01-25 Ktb Tumorforschungsgesellschaft Mbh Acylglycerophospholipides pour traiter des troubles associes au cancer

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BORTOLOTTI ET AL: "Fish oil supplementation does not alter energy efficiency in healthy males", CLINICAL NUTRITION, CHURCHILL LIVINGSTONE, LONDON, GB, vol. 26, no. 2, 30 March 2007 (2007-03-30), pages 225 - 230, XP022004929, ISSN: 0261-5614 *
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U.S. NATIONAL INSTITUTES OF HEALTH: "Safety & Efficacy of Omega-3 Fish Oil in Overweight Children & Adolescents", CLINICAL TRIALS.GOV - INTERNET ARTICLE, 12 March 2007 (2007-03-12), XP002496341, Retrieved from the Internet <URL:http://clinicaltrials.gov/ct2/show/NCT00447291?term=SAFETY+%26+EFFICACY+OF+OMEGA-3+FISH+OIL&rank=1> [retrieved on 20080917] *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011050474A1 (fr) 2009-10-29 2011-05-05 Acasti Pharma, Inc. Compositions de phospholipides thérapeutiques concentrées
US10617702B2 (en) 2009-10-29 2020-04-14 Acasti Pharma Inc. Concentrated therapeutic phospholipid compositions
EP2493478A1 (fr) * 2009-10-29 2012-09-05 Acasti Pharma, Inc. Compositions de phospholipides thérapeutiques concentrées
US10130644B2 (en) 2009-10-29 2018-11-20 Acasti Pharma Inc. Concentrated therapeutic phospholipid compositions
EP2493478A4 (fr) * 2009-10-29 2013-02-27 Acasti Pharma Inc Compositions de phospholipides thérapeutiques concentrées
EP3335713A1 (fr) * 2009-10-29 2018-06-20 Acasti Pharma, Inc. Compositions de phospholipides thérapeutiques concentrées
US9475830B2 (en) 2009-10-29 2016-10-25 Acasti Pharma Inc. Concentrated therapeutic phospholipid compositions
FR2955461A1 (fr) * 2010-01-27 2011-07-29 Polaris Ingredient nutritionnel riche en dha et epa
EP2361513A1 (fr) * 2010-01-27 2011-08-31 Polaris Ingredient nutritionnel riche en DHA et EPA
US9119826B2 (en) 2011-02-16 2015-09-01 Pivotal Therapeutics, Inc. Omega 3 fatty acid for use as a prescription medical food and omega 3 fatty acid diagniostic assay for the dietary management of cardiovascular patients with cardiovascular disease (CVD) who are deficient in blood EPA and DHA levels
WO2012112520A1 (fr) * 2011-02-16 2012-08-23 Pivotal Therapeutics, Inc. Préparations comprenant des acides gras oméga-3 et un agent anti-obésité pour la réduction du poids corporel chez les patients atteints d'une maladie cardiovasculaire et chez les diabétiques
US8951514B2 (en) 2011-02-16 2015-02-10 Pivotal Therapeutics Inc. Statin and omega 3 fatty acids for reduction of apolipoprotein-B levels
US8715648B2 (en) 2011-02-16 2014-05-06 Pivotal Therapeutics Inc. Method for treating obesity with anti-obesity formulations and omega 3 fatty acids for the reduction of body weight in cardiovascular disease patients (CVD) and diabetics
US8952000B2 (en) 2011-02-16 2015-02-10 Pivotal Therapeutics Inc. Cholesterol absorption inhibitor and omega 3 fatty acids for the reduction of cholesterol and for the prevention or reduction of cardiovascular, cardiac and vascular events
JP2014505730A (ja) * 2011-02-16 2014-03-06 ピヴォタル セラピューティクス インコーポレイテッド 心血管疾患患者（ＣＶＤ）および糖尿病患者における体重を減らすための、ω３脂肪酸および抗肥満剤を含む製剤
WO2012155094A1 (fr) * 2011-05-12 2012-11-15 Mycell Technologies, Llc Formulations de phospholipide comprenant des acides gras oméga
WO2013122622A1 (fr) * 2012-02-14 2013-08-22 Pivotal Therapeutics, Inc. Méthode pour traiter l'obésité à l'aide de formulations anti-obésité et d'acides gras oméga-3 pour la réduction du poids corporel chez des patients atteints de maladies cardiovasculaires (mcv) et des diabétiques
EP2930246A1 (fr) 2014-04-07 2015-10-14 QIAGEN GmbH Nouveaux polymorphismes nucléotidiques simples associés à diverses maladies et troubles
US10631564B2 (en) 2015-06-19 2020-04-28 University Of Southern California Enterically coated microparticle compositions and methods for modified nutrient delivery
US10744070B2 (en) 2015-06-19 2020-08-18 University Of Southern California Enteral fast access tract platform system
CN111902053A (zh) * 2017-12-21 2020-11-06 阿克海洋生物南极股份公司 溶血磷脂酰胆碱组合物
US11065267B2 (en) * 2017-12-21 2021-07-20 Aker Biomarine Antarctic As Lysophosphatidylcholine compositions
WO2020177728A1 (fr) * 2019-03-05 2020-09-10 四川国为制药有限公司 Composition d'acides gras et leur application
US11744869B1 (en) * 2023-01-05 2023-09-05 King Abdulaziz University Compositions and methods for treatment of addiction withdrawal symptoms

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